title: Synthesis of oseltamivir and tamiphosphor from N-acetyl-D-glucosamine.
abstract: Using N-acetyl-D-glucosamine as a starting material, the anti-influenza drugs oseltamivir and tamiphosphor were synthesized via a pivotal intermediate of aldehyde 8. An intramolecular Horner-Wadsworth-Emmons reaction was utilized to construct the highly functionalized cyclohexene ring. The existing N-acetyl group was transformed into an azido group for the subsequent aziridination, followed by implantation of a 3-pentoxy group of the desired stereochemistry.
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei 106, Taiwan. jmfang@ntu.edu.tw.
authors.forename: Chih-An
authors.initials: CA
authors.lastname: Chen
authors.forename: Jim-Min
authors.initials: JM
authors.lastname: Fang
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D053139:Oseltamivir / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D010757:Phosphorous Acids / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000998:Antiviral Agents; D010757:Phosphorous Acids; C530824:tamiphosphor; D053139:Oseltamivir; D000117:Acetylglucosamine